Computational output dataset for monoterpene glycoside hydrolysis: Supplement to 10.5281/zenodo.5346588

Computational data resulting from optimisation and vibrational analysis of monoterpenes, geraniol and linalool, resulting from acid-catalysed hydrolysis of geraniol glucoside. Supplementary dataset for the computation described in:

Hixson, Josh, Pisaniello, Lisa, Parker, Mango, Grebneva, Yevgeniya, Bilogrevic, Eleanor, Stegmann, Robin, & Francis, Leigh. (2021, August 31). Methods for predicting and assessing flavour evolution during white wine ageing. https://doi.org/10.5281/zenodo.5346589

Structures were drawn in Avogadro (version 1.2.0), then optimised (UFF) and systematic rotor conformer search performed, with the resulting geometry used to create initial input files for GAMESS (Linux distribution, version 2019 R2, University of Iowa, USA) running on the University of South Australia’s High Performance Compute Cluster. Calculations were first performed for molecules in the gas phase (RHF/3-21G) to provide starting geometries which were then used as the input for density functional theory (B3LYP/6-311G(d)) equilibrium geometry calculations in water (SMD solvent model). Local minima were confirmed by vibrational analysis and the presence of all real frequencies. Each calculation was performed in parallel across eight cores.

The chemical structures input into Avagadro and the naming used in computational files can be found in 'starting_structures_naming.png' and the scheme of glucoside hydrolysis and rearrangement from the original manuscript has been re-published here as 'glycoside_hydrolysis_scheme.png'. Two computational output files (.log) are present for each structure: an output of the geometry optimisation ending in '_B3LYP_6311G_aq.log', and; the optimised geometry analysed by vibrational analysis, including thermochemistry, denoted with '_vibrational.log'. 

The compounds, compound file naming (starting_structures_naming.png) and structure numbering in the original work (glycoside_hydrolysis_scheme.png) are as follows: geraniol glucoside, geraniol_gluc, compound 1; protonated geraniol glucoside, geraniol_gluc_protonated, compound 2; linalyl or geranyl cation (identical structures found after geometry optimisation), linalyl_cation or geranyl cation, compound 3, protonated geraniol, geraniol_protonated, compound 4; geraniol, geraniol, compound 5; protonated linalool, linalool_protonated, compound 6; linalool, linalool, compound 7.